US9980893B2ActiveUtilityA1
Dye composition comprising a 1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-amine compound
Est. expiryDec 20, 2033(~7.4 yrs left)· nominal 20-yr term from priority
A61Q 5/10C07D 471/04A61Q 5/065A61K 2800/4324A61K 8/494
59
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Claims
Abstract
The invention relates to a 1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-amine compound of formula (I) below, addition salts thereof, optical isomers, geometrical isomers and tautomers thereof and/or solvates thereof: in which: .R 2 , R 3 , R 4 , R 5 , and R 7 independently represent: a hydrogen or halogen atom; a C 1 -C 4 alkyl radical; a C 1 -C 4 hydroxyalkyl radical; a carboxyl radical; a (C 1 -C 4 )alkoxycarbonyl radical; .R1 and R6, which may be identical or different, represent: hydrogen atom; C 1 -C 10 and preferably Ci-C6 alkyl radical,—optionally interrupted with one or more heteroatoms chosen from O and S or with one or more groups—NR and/or—optionally terminating with at least one group—NX 1 X 2 or at least one group —OX 3 , .X 1 and X2 independently denote—a hydrogen atom, a linear C 1 -C 6 alkyl radical, a branched C 3 -C 6 alkyl radical, a linear C 1 -C 6 hydroxyalkyl radical or a branched C 3 -C 6 hydroxyalkyl radical, X1 and X2 may form, with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, in which one of the ring members may be a heteroatom chosen from O, S and N; the said heterocycle possibly being substituted with one or more linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl radicals, .X3 denotes—a hydrogen atom—a linear C1-C4 or branched C3-C4 alkyl radical, and .R denotes—a hydrogen atom—a linear C1-C4 alkyl radical.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound chosen from those of formula (I) or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof:
wherein:
R 2 , R 3 , R 4 , R 5 , and R 7 , which are identical or different, are independently chosen from:
a hydrogen or halogen atom;
a C 1 -C 4 alkyl group;
a C 1 -C 4 hydroxyalkyl group;
a carboxyl group; or
a (C 1 -C 4 )alkoxycarbonyl group;
R 1 and R 6 , which are identical or different, are chosen from:
a hydrogen atom; or
a C 1 -C 10 or C 1 -C 6 alkyl group, optionally interrupted with at least one heteroatom chosen from O, S, or at least one —NR group, and/or optionally terminated with at least one —NX 1 X 2 group or a —OX 3 group,
X 1 and X 2 , which are identical or different, are independently chosen from:
a hydrogen atom;
a linear C 1 -C 6 alkyl group;
a branched C 3 -C 6 alkyl group;
a linear C 1 -C 6 hydroxyalkyl group; or
a branched C 3 -C 6 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, wherein at least one ring member is optionally a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group;
X 3 is chosen from:
a hydrogen atom; or
a linear C 1 -C 4 or branched C 3 -C 4 alkyl group; and
R is chosen from:
a hydrogen atom; or
a linear C 1 -C 4 alkyl group.
2. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein R 2 , R 3 , R 4 , R 5 , and R 7 , which may be identical or different, are chosen from a hydrogen atom or a C 1 -C 4 alkyl group.
3. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein R 3 , R 4 , R 5 , and R 7 each represent a hydrogen atom.
4. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein:
X 1 and X 2 independently denote:
a linear C 1 -C 4 alkyl group or a branched C 3 -C 4 alkyl group, or
a linear C 1 -C 4 hydroxyalkyl group or a branched C 3 -C 4 hydroxyalkyl group,
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 7-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group.
5. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein:
X 3 is a hydrogen atom; and
R is chosen from a hydrogen atom or a methyl group.
6. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 5 , wherein the saturated or unsaturated 5- to 7-membered heterocyclic group wherein at least one of the ring members is optionally substituted with a heteroatom chosen from O, S, or N is chosen from imidazole, piperazine, pyrrolidine, morpholine, or piperidine rings.
7. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein:
X 3 is a hydrogen atom; and
R is a hydrogen atom.
8. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein R 1 and R 6 are identical and are chosen from a hydrogen atom or a C 1 -C 6 alkyl group, optionally terminating with at least one group chosen from a —NX 1 X 2 group or an —OH group,
wherein X 1 and X 2 are independently chosen from:
a linear C 1 -C 4 alkyl group;
a branched C 3 -C 4 alkyl group;
a linear C 1 -C 4 hydroxyalkyl group; or
a branched C 3 -C 4 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 7-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group.
9. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein R 1 and R 6 are identical and are chosen from a hydrogen atom or a C 1 -C 6 alkyl group, optionally terminating with one group chosen from a —NX 1 X 2 group or an —OH group,
wherein X 1 and X 2 are independently chosen from:
a linear C 1 -C 4 alkyl group;
a branched C 3 -C 4 alkyl group;
a linear C 1 -C 4 hydroxyalkyl group; or
a branched C 3 -C 4 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 7-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group.
10. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein the compound is chosen from:
or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof.
11. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 wherein R 1 and R 6 are identical and are chosen from a C 1 -C 6 alkyl group interrupted with an oxygen atom or an NH group, and optionally terminated with at least one group chosen from an —NX 1 X 2 group or an —OH group,
wherein X 1 and X 2 are independently chosen from:
a linear C 1 -C 4 alkyl group;
a branched C 3 -C 4 alkyl group;
a linear C 1 -C 4 hydroxyalkyl group; or
a branched C 3 -C 4 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 7-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group.
12. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein the compound is chosen from:
or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof.
13. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein R 1 and R 6 are different and are independently chosen from a hydrogen atom or a C 1 -C 6 alkyl group, optionally terminated with at least one group chosen from an NX 1 X 2 group or an OH group,
wherein X 1 and X 2 are independently chosen from:
a linear C 1 -C 4 alkyl group;
a branched C 3 -C 4 alkyl group;
a linear C 1 -C 4 hydroxyalkyl group; or
a branched C 3 -C 4 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 7-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group.
14. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein R 1 and R 6 are different and are independently chosen from a hydrogen atom or a C 1 -C 6 alkyl group, optionally terminated with an OH group.
15. The 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound according to claim 1 , wherein the compound is chosen from:
or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof.
16. A composition for dyeing keratin fibers, the composition comprising, in a medium that is suitable for dyeing keratin fibers, at least one 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound chosen from those of formula (I) or the addition salts thereof, the optical isomers or geometrical isomers thereof, or the tautomers and/or solvates thereof:
wherein:
R 2 , R 3 , R 4 , R 5 , and R 7 , which are identical or different, are independently chosen from:
a hydrogen or halogen atom;
a C 1 -C 4 alkyl group;
a C 1 -C 4 hydroxyalkyl group;
a carboxyl group; or
a (C 1 -C 4 )alkoxycarbonyl group;
R 1 and R 6 , which are identical or different, are chosen from:
a hydrogen atom; or
a C 1 -C 10 or C 1 -C 6 alkyl group, optionally interrupted with at least one heteroatom chosen from O, S, or at least one —NR group, and/or optionally terminated with at least one —NX 1 X 2 group or a —OX 3 group,
X 1 and X 2 , which are identical or different, are independently chosen from:
a hydrogen atom;
a linear C 1 -C 6 alkyl group;
a branched C 3 -C 6 alkyl group;
a linear C 1 -C 6 hydroxyalkyl group; or
a branched C 3 -C 6 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group;
X 3 is chosen from:
a hydrogen atom; or
a linear C 1 -C 4 or branched C 3 -C 4 alkyl group; and
R is chosen from:
a hydrogen atom; or
a linear C 1 -C 4 alkyl group.
17. The composition of claim 16 , wherein the total amount of 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound ranges from about 0.001% to about 10% by weight, relative to the total weight of the composition.
18. The composition of claim 16 , wherein the at least one 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound is chosen from:
or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof.
19. A method for dyeing keratin fibers, the method comprising:
applying to the keratin fibers, alone or in the presence of an oxidizing agent, a composition comprising at least one 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound chosen from those of formula (I) or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof:
wherein:
R 2 , R 3 , R 4 , R 5 , and R 7 , which are identical or different, are independently chosen from:
a hydrogen or halogen atom;
a C 1 -C 4 alkyl group;
a C 1 -C 4 hydroxyalkyl group;
a carboxyl group; or
a (C 1 -C 4 )alkoxycarbonyl group;
R 1 and R 6 , which are identical or different, are chosen from:
a hydrogen atom; or
a C 1 -C 10 or C 1 -C 6 alkyl group; optionally interrupted with at least one heteroatom chosen from O, S, or at least one —NR group and/or optionally terminated with at least one —NX 1 X 2 group or —OX 3 group,
X 1 and X 2 , which are identical or different, are independently chosen from:
a hydrogen atom;
a linear C 1 -C 6 alkyl group;
a branched C 3 -C 6 alkyl group;
a linear C 1 -C 6 hydroxyalkyl group; or
a branched C 3 -C 6 hydroxyalkyl group;
or X 1 and X 2 form, together with the nitrogen atom that bears them, a saturated or unsaturated 5- to 8-membered heterocycle, wherein at least one ring member is optionally substituted with a heteroatom chosen from O, S, or N; and/or the heterocycle is optionally substituted with at least one linear or branched C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl group;
X 3 is chosen from:
a hydrogen atom; or
a linear C 1 -C 4 or branched C 3 -C 4 alkyl group; and
R is chosen from:
a hydrogen atom; or
a linear C 1 -C 4 alkyl group; and
leaving the composition on the fibers for a sufficient time to develop the desired color.
20. The method of claim 19 , wherein the at least one 1,2,3,4-Tetrahydropyrido[2,3-b]pyrazin-7-amine compound is chosen from:
or the addition salts thereof, optical isomers thereof, geometrical isomers thereof, tautomers thereof, or solvates thereof.Cited by (0)
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